732286-45-2Relevant academic research and scientific papers
Synthesis of 4-benzylpyridines via Pd-catalyzed CH3-arylation of 4-picoline
Wu, Jing,Wang, Dadian,Chen, Xiang,Gui, Qingwen,Li, Hua,Tan, Ze,Huang, Genping,Wang, Guangwei
supporting information, p. 7509 - 7512 (2017/09/27)
A highly efficient synthesis of 4-benzylpyridines was developed via Pd-catalyzed C(sp3)-H arylation between 4-picoline and aryl halides. It was found that the best yields were achieved with a simple Pd(PPh3)4 catalyst and Cs2CO3 as the base. Compared with the known methods, our reaction does not require the use of a strong organometallic reagent as the base.
Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen
Sterckx, Hans,De Houwer, Johan,Mensch, Carl,Herrebout, Wouter,Tehrani, Kourosch Abbaspour,Maes, Bert U.W.
supporting information, p. 144 - 153 (2016/04/05)
The methylene group of various substituted 2- and 4-benzylpyridines, benzyldiazines and benzyl(iso)quinolines was successfully oxidized to the corresponding benzylic ketones using a copper or iron catalyst and molecular oxygen as the stoichiometric oxidant. Application of the protocol in API synthesis is exemplified by the alternative synthesis of a precursor to the antimalarial drug Mefloquine. The oxidation method can also be used to prepare metabolites of APIs which is illustrated for the natural product papaverine. ICP-MS analysis of the purified reaction products revealed that the base metal impurity was well below the regulatory limit.
Convenient methods for the synthesis of d4, d2 and d6 isotopomers of 4-(4-fluorobenzyl)piperidine
Proszenyak, Agnes,Agai, Bela,Tarkanyi, Gabor,Vida, Laszlo,Faigl, Ferenc
, p. 421 - 427 (2007/10/03)
Pure 4-(4-fluoro-[2,3,5,6-2H4]benzyl)piperidine was prepared via the Grignard reaction of 4-fluoro-[2,3,5,6-2H 4]bromobenzene and pyridine-4-aldehyde followed by consecutive deoxygenation and heteroatomic ring saturation in the presence of palladium on carbon catalyst. An improved method for the catalytic H/D exchange in benzylic positions of 4-(4-fluorobenzyl)piperidine and its d4 derivative has also been described. Copyright
Convenient, benign and scalable synthesis of 2- and 4-substituted benzylpiperidines
Agai, Bela,Proszenyak, Agnes,Tarkanyi, Gabor,Vida, Laszlo,Faigl, Ferenc
, p. 3623 - 3632 (2007/10/03)
A short, scalable and environmentally benign synthesis of 2- and 4-substituted benzylpiperidines has been developed. The method is based on the temperature-programmed consecutive deoxygenation and heteroaromatic ring saturation of aryl(pyridin-2-yl)- and aryl(pyridin-4-yl)methanols and aryl(pyridin-4-yl)methanones in the presence of Pd/C catalyst. The crucial roles of the temperature, the acidity and the substrate structure in the change of selectivity have been demonstrated by isolation of several substituted aryl(piperidine)methanols. The carbinols and ketones were prepared from commercially available pyridinecarbaldehydes or 4-cyanopyridine and substituted bromobenzenes via organometallic intermediates. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
